Diastereopure Synthesis of Novel Cyclohexane-Ring-Based Constrained Lanthionine and α-Methyllanthionine through an SN2 Reaction with a β-Bromoalanine as a Key Step,Synlett

当前位置： X-MOL 学术 › Synlett › 论文详情

Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)

Diastereopure Synthesis of Novel Cyclohexane-Ring-Based Constrained Lanthionine and α-Methyllanthionine through an SN2 Reaction with a β-Bromoalanine as a Key Step
Synlett ( IF 1.7 ) Pub Date : 2020-01-13 , DOI: 10.1055/s-0039-1690790
Jaime Gracia-Vitoria , Ángel Carretero , Iñaki Osante ₁ , Carlos Cativiela ₁

Affiliation

Here we report the diastereopure synthesis of a novel protected lanthionine derivative substituted with a cyclohexane ring as well as the diastereopure synthesis of an α-methyllanthionine derivative. By starting from enantiopure α,β-cyclohexane-substituted cystine, or α-methylcysteine, we designed a straightforward route that permits the preparation of orthogonally protected modified lanthionines in diastereopure form. The key step of the methodology is the formation of a thioether bond through the use of an β-bromoalanine derivative. The strategy developed should be valuable in the preparation of a wide range of modified constrained lanthionines that might be finally attached to a peptide sequence, which would be especially useful in the syntheses of novel lantibiotics.

中文翻译：

以β-溴丙氨酸为关键步骤通过SN2反应合成新型环己烷环基受限羊毛硫氨酸和α-甲基羊毛硫氨酸的非对映纯

在这里，我们报告了一种被环己烷环取代的新型受保护羊毛硫氨酸衍生物的非对映纯合成以及 α-甲基羊毛硫氨酸衍生物的非对映纯合成。通过从对映纯的 α,β-环己烷取代的胱氨酸或 α-甲基半胱氨酸开始，我们设计了一条简单的路线，允许以非对映纯形式制备正交保护的改性羊毛硫氨酸。该方法的关键步骤是通过使用 β-溴丙氨酸衍生物形成硫醚键。所开发的策略在制备各种可能最终连接到肽序列的修饰受限羊毛硫氨酸方面应该是有价值的，这在新型羊毛硫抗生素的合成中尤其有用。

更新日期：2020-01-13

点击分享查看原文

点击收藏

阅读更多本刊新发论文本刊介绍/投稿指南